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Caribbean Islands

$164+ Cheap flights from Madison (MSN) to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap flight deals from Madison to Caribbean Islands

Keep the following information in mind while searching for Madison to Caribbean Islands flight deals. Data was last updated August 20, 2025.

Round-trip from

$215
(American Airlines)

One-way from

$164
(Delta)

Popular in

December

Cheapest in

September

Average price

$524
From Madison Truax Field to Caribbean Islands
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One-way flight from Madison Truax Field to Caribbean Islands
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Highest demand for flights based on searches. 2% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Madison to Caribbean Islands

Cheapest flights from Madison to Caribbean Islands
Explore the most affordable flight options available from Madison to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/181:00 pmMSN - SJU
2 stops9h 54mAmerican Airlines
Wed 10/225:30 amSJU - MSN
1 stop7h 45mAmerican Airlines
Deal found 8/20$215
This American Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/173:51 pmMSN - SJU
2 stops18h 20mAmerican Airlines
Sat 9/204:45 pmSJU - MSN
1 stop7h 25mAmerican Airlines
Deal found 8/19$245
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/95:45 amMSN - SJU
1 stop9h 30mDelta
Wed 11/127:00 amSJU - MSN
2 stops11h 36mDelta
Deal found 8/17$260
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/205:08 pmMSN - SJU
2 stops17h 03mAmerican Airlines
Wed 9/245:25 pmSJU - MSN
2 stops17h 34mAmerican Airlines
Deal found 8/18$275
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/118:25 amMSN - SJU
2 stops11h 57mUnited Airlines
Fri 11/148:10 amSJU - MSN
1 stop7h 53mUnited Airlines
Deal found 8/19$278
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/298:10 amMSN - SJU
2 stops14h 27mAmerican Airlines
Tue 10/75:30 amSJU - MSN
1 stop12h 09mAmerican Airlines
Deal found 8/18$282
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/76:20 amMSN - SJU
2 stops16h 17mAmerican Airlines
Fri 9/124:43 pmSJU - MSN
2 stops17h 22mAmerican Airlines
Deal found 8/18$297
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/118:25 amMSN - SJU
2 stops11h 57mUnited Airlines
Tue 11/112:05 amSJU - MSN
2 stops13h 58mUnited Airlines
Deal found 8/17$300
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/118:25 amMSN - SJU
2 stops11h 57mUnited Airlines
Thu 11/132:20 pmSJU - MSN
1 stop10h 25mUnited Airlines
Deal found 8/17$305
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/810:21 amMSN - SJU
1 stop11h 26mAmerican Airlines
Tue 11/116:44 amSJU - MSN
1 stop17h 10mAmerican Airlines
Deal found 8/17$312
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:00 amMSN - SJU
2 stops15h 56mAmerican Airlines
Thu 11/136:42 pmSJU - MSN
2 stops16h 39mAmerican Airlines
Deal found 8/17$313
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/96:30 amMSN - SJU
1 stop7h 10mUnited Airlines
Tue 11/112:05 amSJU - MSN
2 stops13h 58mUnited Airlines
Deal found 8/17$335

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 20, 2025.
Use the filters below to find and compare flights from Madison to Caribbean Islands that are best for you.

Fly from

Madison

Fly to

Caribbean Islands

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 11/11

7:00 am-11:17 pm

2 stops14h 17m

San Juan Luis Munoz Marin Intl

Fri 11/14

7:30 am-4:35 pm

1 stop11h 05m

$215

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 9/17

3:51 pm-11:11 am

2 stops18h 20m

San Juan Luis Munoz Marin Intl

Sat 9/20

4:45 pm-9:59 am

2 stops18h 14m

$215

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 10/18

1:00 pm-11:54 pm

2 stops9h 54m

San Juan Luis Munoz Marin Intl

Wed 10/22

5:30 am-12:15 pm

1 stop7h 45m

$215

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 1/31

10:38 am-12:05 am

2 stops11h 27m

San Juan Luis Munoz Marin Intl

Thu 2/5

7:20 am-1:26 pm

1 stop8h 06m

$245

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 2/3

6:13 am-8:50 pm

2 stops12h 37m

San Juan Luis Munoz Marin Intl

Tue 2/10

2:25 pm-11:42 pm

1 stop11h 17m

$245

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Wed 11/19

6:30 am-4:02 pm

1 stop7h 32m

Punta Cana

Tue 11/25

2:55 pm-8:35 pm

1 stop7h 40m

$361

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Sat 11/15

3:55 pm-11:55 am

2 stops18h 00m

Punta Cana

Fri 11/21

5:52 pm-9:56 am

1 stop18h 04m

$366

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Sun 12/7

6:38 am-4:39 pm

1 stop8h 01m

Punta Cana

Thu 12/11

2:05 pm-10:20 am

1 stop22h 15m

$368

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Sun 12/7

6:38 am-4:39 pm

1 stop8h 01m

Punta Cana

Sun 12/14

6:20 pm-11:41 pm

1 stop7h 21m

$391

MadisonSaint Thomas Island

MSN - STT

MSNSTT

Madison Truax Field

Thu 10/23

4:29 pm-12:00 pm

2 stops18h 31m

Saint Thomas Island Cyril E King

Mon 10/27

5:20 pm-10:08 am

2 stops17h 48m

$509

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 48 results
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Best time to book a flight from Madison to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Madison with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Madison to Caribbean Islands

What is the cheapest month to book a flight from Madison to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $254). Flying from Madison to Caribbean Islands in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MSN to EPX?

Find hourly flight availability from Madison to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 20, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Madison to Caribbean Islands as you normally would.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated August 20, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Madison to Caribbean Islands. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,928 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Madison to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Madison to Caribbean Islands?

    Madison Truax Field (MSN) is the airport you will fly out of if you book a flight from Madison to Caribbean Islands. It is only a 5.4 mi journey to Truax Field (MSN) from Madison’s city center.

  • How long is the flight from Madison to Caribbean Islands?

    A quick flight from Madison to Caribbean Islands can take about 7h 32m. Delta provides one of the quickest options available for as low as $361. There are 2090 mi between Madison and Caribbean Islands. This flight may include one or multiple stops.

  • What are the most popular routes from Madison to Caribbean Islands?

    While some choose either Madison Truax Field - Punta Cana or Madison Truax Field - Oranjestad Reina Beatrix, Madison Truax Field - San Juan Luis Munoz Marin Intl is the most popular route from Madison to Caribbean Islands.

  • Can I find deals for flights from Madison to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Madison to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Caribbean Islands.

  • Can I find deals for business class flights from Madison to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Madison to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Madison to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $254). Flying from Madison to Caribbean Islands in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Madison to Caribbean Islands

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Top 3 airlines flying from Madison to Caribbean Islands

Discover the top 3 airlines that operate flights from Madison to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$740FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$271Average$649FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$331Average$659FlexibilityNo cancel feeOn-time69%

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